(2R,3S,4S,5S,7S,10S,12S,13Z)-11-(tert-butyldimethylsilanyloxy)-3,5-[(R)-4-methoxybenzylidenedioxy]-7-methoxymethoxy-2,4,10,12-tetramethyl-14-trimethylsilanylpentadeca-13-en-8-yn acid methyl ester

Base Information

Chemical Name:(2R,3S,4S,5S,7S,10S,12S,13Z)-11-(tert-butyldimethylsilanyloxy)-3,5-[(R)-4-methoxybenzylidenedioxy]-7-methoxymethoxy-2,4,10,12-tetramethyl-14-trimethylsilanylpentadeca-13-en-8-yn acid methyl ester
CAS No.:851889-80-0
Molecular Formula:C₃₉H₆₆O₈Si₂
Molecular Weight:719.119
Hs Code.:

(2R,3S,4S,5S,7S,10S,12S,13Z)-11-(tert-butyldimethylsilanyloxy)-3,5-[(R)-4-methoxybenzylidenedioxy]-7-methoxymethoxy-2,4,10,12-tetramethyl-14-trimethylsilanylpentadeca-13-en-8-yn acid methyl ester

Synonyms:(2R,3S,4S,5S,7S,10S,12S,13Z)-11-(tert-butyldimethylsilanyloxy)-3,5-[(R)-4-methoxybenzylidenedioxy]-7-methoxymethoxy-2,4,10,12-tetramethyl-14-trimethylsilanylpentadeca-13-en-8-yn acid methyl ester

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Chemical Property of (2R,3S,4S,5S,7S,10S,12S,13Z)-11-(tert-butyldimethylsilanyloxy)-3,5-[(R)-4-methoxybenzylidenedioxy]-7-methoxymethoxy-2,4,10,12-tetramethyl-14-trimethylsilanylpentadeca-13-en-8-yn acid methyl ester

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Technology Process of (2R,3S,4S,5S,7S,10S,12S,13Z)-11-(tert-butyldimethylsilanyloxy)-3,5-[(R)-4-methoxybenzylidenedioxy]-7-methoxymethoxy-2,4,10,12-tetramethyl-14-trimethylsilanylpentadeca-13-en-8-yn acid methyl ester

There total 23 articles about (2R,3S,4S,5S,7S,10S,12S,13Z)-11-(tert-butyldimethylsilanyloxy)-3,5-[(R)-4-methoxybenzylidenedioxy]-7-methoxymethoxy-2,4,10,12-tetramethyl-14-trimethylsilanylpentadeca-13-en-8-yn acid methyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 83.0%

: 851889-79-7
(2R,3S,4S,5S,7S,10S,11S,12S,13Z)-11-(tert-butyldimethylsilanyloxy)-3,5-[(R)-4-methoxybenzylidenedioxy]-7-hydroxy-2,4,10,12-tetramethyl-14-trimethylsilanylpentadeca-13-en-8-yn acid methyl ester

: 107-30-2
chloromethyl methyl ether

: 851889-80-0
(2R,3S,4S,5S,7S,10S,12S,13Z)-11-(tert-butyldimethylsilanyloxy)-3,5-[(R)-4-methoxybenzylidenedioxy]-7-methoxymethoxy-2,4,10,12-tetramethyl-14-trimethylsilanylpentadeca-13-en-8-yn acid methyl ester

Guidance literature:: With dmap; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20 ℃; for 8h;
DOI:10.1021/ja043168j

Reference yield:

: 851889-68-4
(3E,5S,6S,7R)-6,8-[(R)-4-methoxy-benzylidenedioxy]-4,5,7-trimethyl-oct-3-enoic acid methyl ester

: 851889-80-0
(2R,3S,4S,5S,7S,10S,12S,13Z)-11-(tert-butyldimethylsilanyloxy)-3,5-[(R)-4-methoxybenzylidenedioxy]-7-methoxymethoxy-2,4,10,12-tetramethyl-14-trimethylsilanylpentadeca-13-en-8-yn acid methyl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: ozone; pyridine / methanol / -78 °C

1.2: 95 percent / dimethyl sulfide / methanol / -78 - 0 °C

2.1: diisopropylethyl amine / CH₂Cl₂ / 0.08 h / -78 °C

2.2: Bu₂BOTf / CH₂Cl₂ / 0.75 h / -78 °C

2.3: 76 percent / CH₂Cl₂ / 1 h / -78 °C

3.1: 95 percent / SmI₂ / tetrahydrofuran / 4 h / -10 °C

4.1: KOH / methanol / 20 °C

4.2: 20 percent / silica gel / methanol; hexane

5.1: PPTS / CH₂Cl₂

6.1: 0.47 g / RuCl₂(PPh₃)3 / benzene / 8 h / 20 °C

7.1: NaClO₂; NaH₂PO₄*H₂₀; 2-methyl-2-butene / 2-methyl-propan-2-ol / 2 h / 20 °C

8.1: 0.44 g / benzene; methanol; hexane / 0.25 h

9.1: 83 percent / diisopropylethylamine; DMAP / CH₂Cl₂ / 8 h / 0 - 20 °C

With pyridine; dmap; potassium hydroxide; sodium chlorite; sodium dihydrogenphosphate; tris(triphenylphosphine)ruthenium(II) chloride; samarium diiodide; 2-methyl-but-2-ene; pyridinium p-toluenesulfonate; ozone; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; tert-butyl alcohol; benzene; 3.1: Evans-Tischenko reduction;
DOI:10.1021/ja043168j

Reference yield:

: 851889-73-1
(2S,3R,4R,7S,10S,11R,12S,13Z)-11-(tert-butyldimethylsilanyloxy)-1,3-[(R)-4-methoxybenzylidenedioxy]-7-hydroxy-2,4,10,12-tetramethyl-14-trimethylsilanylpentadec-13-en-8-yn-5-one

: 851889-80-0
(2R,3S,4S,5S,7S,10S,12S,13Z)-11-(tert-butyldimethylsilanyloxy)-3,5-[(R)-4-methoxybenzylidenedioxy]-7-methoxymethoxy-2,4,10,12-tetramethyl-14-trimethylsilanylpentadeca-13-en-8-yn acid methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: 95 percent / SmI₂ / tetrahydrofuran / 4 h / -10 °C

2.1: KOH / methanol / 20 °C

2.2: 20 percent / silica gel / methanol; hexane

3.1: PPTS / CH₂Cl₂

4.1: 0.47 g / RuCl₂(PPh₃)3 / benzene / 8 h / 20 °C

5.1: NaClO₂; NaH₂PO₄*H₂₀; 2-methyl-2-butene / 2-methyl-propan-2-ol / 2 h / 20 °C

6.1: 0.44 g / benzene; methanol; hexane / 0.25 h

7.1: 83 percent / diisopropylethylamine; DMAP / CH₂Cl₂ / 8 h / 0 - 20 °C

With dmap; potassium hydroxide; sodium chlorite; sodium dihydrogenphosphate; tris(triphenylphosphine)ruthenium(II) chloride; samarium diiodide; 2-methyl-but-2-ene; pyridinium p-toluenesulfonate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; tert-butyl alcohol; benzene; 1.1: Evans-Tischenko reduction;
DOI:10.1021/ja043168j